New process for introducing sulphocyanic groups in aliphatic compounds



Patented May 24, 1932 UNITED STATES PATENT OFFICE HANS PAUL KAUFMANN, OF JENA, GERMANY, ASSIGNOR TO I. G. FARIBENINDUSTRIE AKTIENGESELLSCHAFT, 0F FRANKFORT-ON-THE-MAIN, GERMANY, A CORPORATION OF GERMANY NEW PROCESS FOR INTRODUCING SULPHOCYANIC GROUPS IN ALIIHATIC COMPOUNDS 1% Drawing. Original application filed August 21, 1926, Serial No. 130,770, and in Germany August 27,

1925. Divided and. this application filed November 30, 1928.

This application is a division of my application Serial No. 130,770, filed August 21, 1926.

The present invention relates to a new process for introducing sulphocyanic groups into organic compounds.

My new process consists in causing an alkali metal salt of sulphocyanic acid in solution together with a halogen to react on an organic compound.

The reaction can be effected in an aqueous or an acid medium, the new process being therefore of Wide application and allowing the production of various organic sulphocyanic compounds of difierent classes on a technical scale.

It is possible to introduce one or more sulphocyanic groups into aliphatic compounds according to the capability of these compounds to add sulphocyanic groups on double or triple valance bonds in their molecule.

In order to further illustrate my invention the following example is given, the parts being by weight and all temperatures in centigrade degrees, but it is understood, that my invention is not limited to the particular products or reacting conditions mentioned therein.

E wample (a) 25 parts of sodium sulphocyanide are dissolved in 150 parts of acetic acid (of 96% CHr-SUN Hz-SON is soluble in water and the usual organic sol- Serial No. 322,965.

vents and melts in a pure state at 90 (see Archiv der Pharmazie (2) vol. 85, page 1).

(b) 10 parts of sodium sulphocyanide are dissolved in 60 parts of hydrochloric acid of 15% strength. Then a strong current of ethylene is allowed to pass through the well cooled solution and 6 parts of bromine, dissolved in a suitable amount of hydrochloric acid, are dropped in slowly. The formed ethylene-disulphocyanide is isolated, as described above.

In the same manner sulphocyanic groups may be introduced into acetylene.

I claim:

1. A process which comprises causing an alkali metal salt of sulphocyanic acid in a dissolved form and a halogen to act on an aliphatic compound of an unsaturated character.

2. A process which comprises causing an alkali metal salt of sulphocyanic acid in a dissolved form and a halogen to act in an acidic medium on an aliphatic compound of an unsaturated character.

3. The new process which comprises causing chlorine and a solution of'sodium sulphocyanide in acetic acid to act upon ethylene.

4. The new process which comprises causing bromine and a solution of sodium sulphocyanide in aqueous hydrochloric acid to act upon ethylene.

5. The new process which comprises passing a current of ethylene and chlorine through a sgllution of sodium sulphocyanide in acetic ac1 6. The new process which comprises passing a current of ethylene through a solution of sodium sulphocyanide in aqueous hydrochloric acid, and then slowly adding bromine dissolved in hydrochloric acid.

In testimony whereof,I afiix my signature. 7 V

HANS PAUL KAUFMANN. 

